Synthesis and Characterization of Aplysinopsin Analogs

AbstractThree aplysinopsin analogs were synthesized by reacting 5-bromo-5-fluoro- and 6-bromoindole-3-carboxaldehyde with either creatinine or 2-imino-1,3-dimethyl-imidazolidin-4-one or 2-imino-1-methyl-3-ethylimidazolidin-4-one Single crystal structures on 5-bromo-4′-de-N-methylaplysinopsin DMF solvate [from creatinine, space group P2 1 /n, lattice parameters a = 13.117(3) A, b = 8.6663(15) A, c = 14.743(3) A, β = 99.538(10)° at 173 K], 5-fluoroaplysinopsin DMF solvate [from 2-imino-1,3-dimethyl-imidazolidin-4-one, space group P2 1 /c, lattice parameters a = 11.114(3) A, b = 19.118(2) A, c = 8.503(2) A, β = 112.290(7)°], and 6-bromoindole-3-carboxaldehyde (space group P2 1 /n, lattice parameters a = 7.657(2) A, b = 7.933(2) A, c = 13.521(3) A, β = 99.046(13)°) have been determined. Characterizations include spectrometric identifications employing IR, UV, HRMS, and 1 H and 13 C NMR. 5-Bromo-4′-de-N-methylaplysinopsin and 5-fluoroaplysinopsin exist in the E configuration.Index AbstractSingle crystal X-ray structural analyses were carried out on 5-bromo-4′-de-N-methylaplysinopsin, 5-fluoroaplysinopsin, and 6-bromoindole-3-carboxaldehyde.[IMAGE]